EP1068865A1 - Utilisation de l'acide 4,6-dimethoxy-indole 2-carboxylique ou de ses dérives pour le traítement de la séborrhée - Google Patents
Utilisation de l'acide 4,6-dimethoxy-indole 2-carboxylique ou de ses dérives pour le traítement de la séborrhée Download PDFInfo
- Publication number
- EP1068865A1 EP1068865A1 EP00401743A EP00401743A EP1068865A1 EP 1068865 A1 EP1068865 A1 EP 1068865A1 EP 00401743 A EP00401743 A EP 00401743A EP 00401743 A EP00401743 A EP 00401743A EP 1068865 A1 EP1068865 A1 EP 1068865A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- radical
- composition
- hydrogen atom
- indole
- dimethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 0 COc1cc([n](*)c(*)c2)c2c(OC)c1 Chemical compound COc1cc([n](*)c(*)c2)c2c(OC)c1 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/008—Preparations for oily skin
Definitions
- the invention relates to the use in a composition or for the preparation of a composition of an effective amount of 4,6-dimethoxy-indole 2-carboxylic acid or its derivatives, the compound or composition being intended for treat seborrhea and associated dermatoses, including acne and / or blackheads and / or blackheads.
- Seborrhea or sebaceous hypersecretion is the cause of skin disorders that are oily skin and oily scalp, aesthetic disorders that can become the bed of dermatological conditions like acne, dermatitis seborrheic, blackheads or even blackheads.
- Acne is one of the diseases most often affecting, and to varying degrees, the juvenile population between 15 and 30 years old. Acne is basically the consequence of two entangled phenomena: sebaceous hypersecretion and disturbance of the keratinization of the pilosebaceous follicle, the consequences of which are the obstruction of the pilosebaceous follicle and the formation of retentional lesions or blackheads. Comedones, as a result of microbial growth, can develop into inflammatory lesions, papules and pustules.
- Seborrheic dermatitis is associated with the proliferation of yeasts of the genus Pityrosporum on the substrate that constitutes sebum for them.
- the sebaceous flow regulation eliminates the initial cause, i.e. the presence excessive sebum, and consequently treats dermatosis.
- isotretinoin is not without serious side effects and therefore remains reserved for the treatment of severe, disabling acne.
- the topical seborrhea treatments have so far proven to be effective and this lack of efficacy is frequently remedied by treatments systemically, especially with isotretinoin or antiandrogens.
- the acid 4,6-dimethoxy-indole 2-carboxylic acid or its derivatives have properties anti-seborrheic and can therefore be used in a composition as active to fight against seborrhea of the skin or scalp, and against the dermatoses which can result therefrom like acne, seborrheic dermatitis, blackheads and / or blackheads.
- the dermatosis associated with seborrhea can in particular be acne and / or blackheads and / or blackheads.
- heterocycle is preferably meant according to the invention a cycle including optionally one or more nitrogen and / or oxygen atoms and particularly pyridine, imidazole, tetrahydrofuran or furan.
- a a particularly preferred heterocycle according to the invention is pyridine.
- C 1 -C 4 alkyl radical is meant according to the invention the acyclic radicals originating from the removal of a hydrogen atom in the molecule of a hydrocarbon, linear or branched having from 1 to 4 carbon atoms and in particular the methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl radicals.
- C 7 -C 12 aralkyl radical preferably means, according to the invention, alkyl-aryl radicals having from 7 to 12 carbon atoms, definition in which the term aryl is understood as an aromatic ring having 5 or 6 atoms of carbon or an aromatic heterocycle having 5 or 6 atoms.
- the aralkyl radical is C 7 -C 10 .
- a particularly preferred aralkyl radical according to the invention is the benzyl radical.
- an optionally substituted phenyl radical it is preferably understood according to the invention the phenyl radical optionally substituted by a cyano group (-CN), a trifluoromethyl group (-CF 3 ), a methoxy radical (-O-CH 3 ) or a halogen atom.
- the halogen atom can be chosen from chlorine, bromine, fluorine, iodine.
- a particularly preferred substituted phenyl radical according to the invention is the phenyl radical substituted by a trifluoromethyl group (-CF 3 ).
- R 1 represents a hydrogen atom or a methyl or ethyl radical.
- R 2 represents a hydrogen atom or a methyl radical.
- R 1 and R 2 are a hydrogen atom.
- the compounds can be used alone or as a mixture.
- the effective amount of compound to be used obviously corresponds to the amount necessary to obtain the desired result. Those skilled in the art are therefore able to assess this effective amount which depends on the nature of the compound used and the person thus treated.
- the compound represents present at a concentration of between 0.001% and 20% by weight relative to the total weight of the composition and preferably of between 0.1% and 5% .
- the compounds of formula (I) can be used in compositions for cosmetic or pharmaceutical use.
- the compounds of formula (I) are used in compositions with cosmetic use.
- compositions according to the invention can be in all forms suitable for topical application, especially in the form of solutions aqueous, hydroalcoholic or oily, of lotion-type dispersions or serum, aqueous, anhydrous or oily gels, liquid consistency emulsions or semi-liquid of the milk type, obtained by dispersing a fatty phase in an aqueous phase (O / W) or vice versa (W / O), suspensions or emulsions of soft, semi-solid or solid consistency of the cream, gel, microemulsions, or microcapsules, microparticles, or Ionic and / or nonionic type vesicular dispersions.
- These compositions are prepared according to the usual methods well known to those skilled in the art. field.
- compositions of the invention may include adjuvants conventionally implemented in the fields considered as bodies oily, organic solvents, thickeners, softeners, antioxidants, opacifiers, stabilizers, anti-foaming agents, perfumes, ionic or non-ionic emulsifiers, fillers, sequestrants, dyes or any other ingredient usually used in cosmetics.
- the proportion of the phase fatty can range from 5 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition.
- Oils, emulsifiers and coemulsifiers used in the composition in the form of an emulsion are chosen among those conventionally used in the cosmetic field or dermatological.
- the emulsifier and possibly the coemulsifier are present in the composition in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition.
- the emulsion may, in addition, contain lipid vesicles.
- mineral oils mineral oils
- vegetable oils liquid fraction of shea butter
- animal oils synthetic oils
- purcellin oil polyisobutene hydrogenated
- silicone oils fluorinated oils
- fluorinated oils perfluoropolyethers
- emulsifiers which can be used in the invention, mention may, for example, be made of polyol fatty acid esters, such as sorbitol fatty esters, such as sorbitan tristearate sold under the name Span 65 by the company ICI, or also fatty esters of glycerol such as glycerol monostearate, or still PEG esters such as PEG-40 stearate sold under the name of Myrj 52 by the company ICI. It can also be emulsifiers silicone such as cetyl dimethicone copolyol sold under the name of Abil EM90 by the company Goldschmidt.
- polyol fatty acid esters such as sorbitol fatty esters, such as sorbitan tristearate sold under the name Span 65 by the company ICI
- glycerol such as glycerol monostearate
- PEG esters such as PEG-40 stearate sold under the name of Myrj 52 by the company ICI
- hydrophilic gelling agents mention may be made of carboxyvinyl polymers (carbomer), acrylic copolymers such as copolymers acrylates / alkylacrylates, glyceryl poly (meth) acrylates such as the product sold under the name of Norgel by Guardian, the polyacrylamides and in particular the mixture of polyacrylamide, C13-14-isoparaffin and Laureth-7, sold under the name of Sepigel 305 by the company Seppic, polysaccharides, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as bentones, metal salts of fatty acids, hydrophobic silica and polyethylenes.
- carboxyvinyl polymers carboxyvinyl polymers
- acrylic copolymers such as copolymers acrylates / alkylacrylates
- glyceryl poly (meth) acrylates such as the product sold under the name of Norgel by Guardian
- compositions of the invention can also comprise active agents, hydrophilic or lipophilic, and in particular active agents capable of supplementing the effect of ascorbic acid in the treatment of seborrhea and associated dermatoses, including acne.
- active agents capable of supplementing the effect of ascorbic acid in the treatment of seborrhea and associated dermatoses, including acne.
- It can be for example anti-inflammatory agents such as benzoyl peroxide, antibiotics, antiseptic agents such as octopirox or keratolytic active agents such as salicylic acid and its derivatives, alpha-hydroxy acids, retinoic acid and its derivatives, retinol and its derivatives.
- hydrophilic active agents it is possible to use, for example, proteins or protein hydrolysates, amino acids, polyols (glycerin, propylene glycol), urea, allantoin, sugars and sugar derivatives, water-soluble vitamins, starch, bacterial or plant extracts, including Aloe Vera, moisturizers.
- tocopherol vitamin E
- essential fatty acids ceramides
- essential oils for example tocopherol (vitamin E) and its derivatives, essential fatty acids, ceramides, essential oils.
- the present invention also relates to a cosmetic treatment process seborrhea and dermatoses associated with seborrhea, such as example acne and / or blackheads and / or blackheads, consisting in applying on the skin and / or scalp, a composition comprising an amount effective of at least one compound corresponding to the general formula (I), to be left the latter in contact with the skin and / or the scalp, and possibly to rinse.
- a cosmetic treatment process seborrhea and dermatoses associated with seborrhea, such as example acne and / or blackheads and / or blackheads, consisting in applying on the skin and / or scalp, a composition comprising an amount effective of at least one compound corresponding to the general formula (I), to be left the latter in contact with the skin and / or the scalp, and possibly to rinse.
- the cosmetic treatment method of the invention aims to treat acne and / or blackheads and / or blackheads.
- the treatment process has the characteristics of a cosmetic process insofar as it improves the aesthetics of the skin by giving it a improved appearance.
- compositions according to the invention are:
- compositions are obtained by the usual techniques commonly used in cosmetics or pharmacy.
- Niosome gel
- This gel is applied to the skin, once or twice a day.
- Niosome lotion
- This lotion is applied to the skin once or twice a day.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Description
R1 et R2, identiques ou différents, représentent :
ledit composé et/ou lesdites compositions étant destinés à traiter la séborrhée de la peau et/ou du cuir chevelu, et/ou les dermatoses associées à la séborrhée.
Pour donner un ordre de grandeur, dans les compositions selon l'invention le composé représente présent à une concentration comprise entre 0,001% et 20% en poids par rapport au poids total de la composition et de préférence comprise entre 0,1% et 5%.
- Chimexane NS® 1,80 g
- Stéaroylglutamate monosodique 0,20 g
- acide 4,6-diméthoxy-indole-2-carboxylique 1,00 g
- Carbomer 0,20 g
- Triéthanolamine qspH = 7
- Conservateurs qs
- Parfums qs
- Eau déminéralisée qsp 100,00 g
- Chimexane NL® 0,475 g
- Cholestérol 0,475 g
- Stéaroylglutamate monosodique 0,050 g
- acide 4,6-diméthoxy-indole-2-carboxylique 2,000 g
- Conservateurs qs
- Colorants qs
- Parfum qs
- Eau déminéralisée qsp 100,000 g
- acide 4,6-diméthoxy-indole-2-carboxylique 2,00 g
- Dowanol PM®** 20,00 g
- Klucel G®* 3,00 g
- Alcool éthylique 40,00 g
- Eau qsp 100,00 g
Claims (13)
- Utilisation dans une composition ou pour la préparation d'une composition, d'une quantité efficace d'au moins un composé répondant à la formule générale (I): dans laquelle
R1 et R2, identiques ou différents, représentent :ses formes acylées ou encore ses sels physiologiquement acceptables pris seuls ou en mélange en toutes proportions ;un atome d'hydrogène,ou un radical alkyle en C1-C6, éventuellement substitué par un radical -OH, -NHR3, -SH, -COOH ou -COOR3, dans lesquels R3 représente un radical alkyle en C1-C4, linéaire ou ramifié,ou un radical aralkyle en C7 - C12 ,ou un radical -CHR4R5, dans lequel R4 et R5 identiques ou différents représentent un atome d'hydrogène ou un radical phényle éventuellement substitué ou encore un hétérocycle ayant 5 ou 6 chaínons ;
ledit composé et/ou lesdites compositions étant destinés à traiter la séborrhée de la peau et/ou du cuir chevelu. - Utilisation dans une composition ou pour la préparation d'une composition, d'une quantité efficace d'au moins un composé répondant à la formule générale (I) : dans laquelle
R1 et R2, identiques ou différents, représentent :ses formes acylées ou encore ses sels physiologiquement acceptables pris seuls ou en mélange en toutes proportions ;un atome d'hydrogène,ou un radical alkyle en C1-C6, éventuellement substitué par un radical -OH, -NHR3, -SH, -COOH ou -COOR3, dans lesquels R3 représente un radical alkyle en C1-C4, linéaire ou ramifié,ou un radical aralkyle en C7 - C12 ,ou un radical -CHR4R5, dans lequel R4 et R5 identiques ou différents représentent un atome d'hydrogène ou un radical phényle éventuellement substitué ou encore un hétérocycle ayant 5 ou 6 chaínons ;
ledit composé et/ou lesdites compositions étant destinés à traiter les dermatoses associées à la séborrhée. - Utilisation dans une composition ou pour la préparation d'une composition, d'une quantité efficace d'au moins un composé répondant à la formule générale (I) : dans laquelle
R1 et R2, identiques ou différents, représentent :ses formes acylées ou encore ses sels physiologiquement acceptables pris seuls ou en mélange en toutes proportions ;un atome d'hydrogène,ou un radical alkyle en C1-C6, éventuellement substitué par un radical -OH, -NHR3, -SH, -COOH ou -COOR3, dans lesquels R3 représente un radical alkyle en C1-C4, linéaire ou ramifié,ou un radical aralkyle en C7 - C12 ,ou un radical -CHR4R5, dans lequel R4 et R5 identiques ou différents représentent un atome d'hydrogène ou un radical phényle éventuellement substitué ou encore un hétérocycle ayant 5 ou 6 chaínons ;
ledit composé et/ou lesdites compositions étant destinés à traiter l'acné et/ou les points noirs et/ou les comédons. - Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que R1 est un atome d'hydrogène ou un radical méthyle ou bien éthyle.
- Utilisation selon la revendication précédente, caractérisée par le fait que R1 est un atome d'hydrogène.
- Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que R2 est un atome d'hydrogène ou un radical méthyle.
- Utilisation selon la revendication précédente, caractérisée par le fait que R2 est un atome d'hydrogène.
- Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que le composé est choisi parmil'acide 4,6-diméthoxy-indole 2-carboxyliquel'acide 4,6-diméthoxy-indole 2-carboxylate de méthylel'acide N-méthyl-4,6-diméthoxy-indole 2-carboxyliquel'acide N-méthyl-4,6-diméthoxy-indole 2-carboxylate de méthylel'acide N-éthyl-4,6-diméthoxy-indole 2-carboxylique.
- Utilisation selon la revendication précédente, caractérisée par le fait que le composé est l'acide 4,6-diméthoxy-indole 2-carboxylique.
- Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que le composé présent est utilisé à une concentration comprise entre 0,001% et 20%, en poids par rapport au poids total de la composition.
- Utilisation selon l'une quelconque des revendications précédentes, caractérisée par le fait que le composé présent est utilisé à une concentration comprise entre 0,1% et 5%, en poids par rapport au poids total de la composition.
- Procédé de traitement cosmétique de la séborrhée et/ou des dermatoses associées à la séborrhée, consistant à appliquer sur la peau et/ou le cuir chevelu, une composition comprenant une quantité efficace d'au moins un composé répondant à la formule générale (I) tel que définie dans l'une quelconque des revendications 1 à 11, à laisser celle-ci en contact avec la peau et/ou le cuir chevelu, et éventuellement à rincer.
- Procédé de traitement cosmétique de l'acné, consistant à appliquer sur la peau une composition comprenant une quantité efficace d'au moins un composé répondant à la formule générale (I) tel que définie dans l'une quelconque des revendications 1 à 11, à laisser celle-ci en contact avec la peau, et éventuellement à rincer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9909269 | 1999-07-16 | ||
| FR9909269A FR2796279B1 (fr) | 1999-07-16 | 1999-07-16 | Utilisation de l'acide 4,6-dimethoxy-indole 2-carboxylique ou de ses derives pour le traitement de la seborrhee |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1068865A1 true EP1068865A1 (fr) | 2001-01-17 |
| EP1068865B1 EP1068865B1 (fr) | 2005-03-16 |
Family
ID=9548200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP00401743A Expired - Lifetime EP1068865B1 (fr) | 1999-07-16 | 2000-06-19 | Utilisation de l'acide 4,6-diméthoxy-indole 2-carboxylique ou de ses dérivés pour le traitement de la séborrhée |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6335359B1 (fr) |
| EP (1) | EP1068865B1 (fr) |
| JP (1) | JP3636044B2 (fr) |
| AT (1) | ATE290850T1 (fr) |
| CA (1) | CA2314539A1 (fr) |
| DE (1) | DE60018647T8 (fr) |
| ES (1) | ES2240026T3 (fr) |
| FR (1) | FR2796279B1 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05002168A (es) * | 2002-08-27 | 2005-05-23 | Galderma Res & Dev | Analogos de vitamina d. |
| AU2003275225A1 (en) * | 2002-09-20 | 2004-04-08 | Genelabs Technologies, Inc. | Novel aromatic compounds possessing antifungal or antibacterial activity |
| WO2007005941A2 (fr) | 2005-07-05 | 2007-01-11 | President And Fellows Of Harvard College | Conjugues cibles sur le foie |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999007351A2 (fr) * | 1997-08-07 | 1999-02-18 | Zeneca Limited | Composes chimiques |
| WO1999012905A1 (fr) * | 1997-09-05 | 1999-03-18 | L'oreal | Composes indole-carboxyliques et leur utilisation comme composes pharmaceutiques |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2963288B2 (ja) * | 1992-01-14 | 1999-10-18 | 株式会社海洋バイオテクノロジー研究所 | 水中有害付着生物防除剤 |
| GB9204365D0 (en) * | 1992-02-28 | 1992-04-08 | Pfizer Ltd | Indoles |
| FR2689898B1 (fr) * | 1992-04-08 | 1994-06-10 | Oreal | Pigments comportant un support inorganique et le produit de reaction d'un derive indolique et d'un derive quinonique, leur procede de preparation et leur utilisation en cosmetique. |
| GB9317096D0 (en) * | 1993-08-17 | 1993-09-29 | Pfizer Ltd | Indoles |
-
1999
- 1999-07-16 FR FR9909269A patent/FR2796279B1/fr not_active Expired - Fee Related
-
2000
- 2000-06-19 AT AT00401743T patent/ATE290850T1/de not_active IP Right Cessation
- 2000-06-19 EP EP00401743A patent/EP1068865B1/fr not_active Expired - Lifetime
- 2000-06-19 DE DE60018647T patent/DE60018647T8/de not_active Expired - Fee Related
- 2000-06-19 ES ES00401743T patent/ES2240026T3/es not_active Expired - Lifetime
- 2000-07-05 CA CA002314539A patent/CA2314539A1/fr not_active Abandoned
- 2000-07-14 US US09/617,039 patent/US6335359B1/en not_active Expired - Fee Related
- 2000-07-17 JP JP2000216711A patent/JP3636044B2/ja not_active Expired - Fee Related
-
2001
- 2001-12-04 US US10/000,293 patent/US6548532B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999007351A2 (fr) * | 1997-08-07 | 1999-02-18 | Zeneca Limited | Composes chimiques |
| WO1999012905A1 (fr) * | 1997-09-05 | 1999-03-18 | L'oreal | Composes indole-carboxyliques et leur utilisation comme composes pharmaceutiques |
Also Published As
| Publication number | Publication date |
|---|---|
| US20020058680A1 (en) | 2002-05-16 |
| EP1068865B1 (fr) | 2005-03-16 |
| DE60018647T2 (de) | 2006-01-19 |
| JP2001058948A (ja) | 2001-03-06 |
| DE60018647T8 (de) | 2006-08-24 |
| FR2796279B1 (fr) | 2001-09-21 |
| ATE290850T1 (de) | 2005-04-15 |
| DE60018647D1 (de) | 2005-04-21 |
| US6548532B2 (en) | 2003-04-15 |
| FR2796279A1 (fr) | 2001-01-19 |
| US6335359B1 (en) | 2002-01-01 |
| JP3636044B2 (ja) | 2005-04-06 |
| CA2314539A1 (fr) | 2001-01-16 |
| ES2240026T3 (es) | 2005-10-16 |
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